Self-Assembly of a [2]Pseudorota[3]catenane in Water

被引：34
|
作者：
Forgan, Ross S. [1 ]
Gassensmith, Jeremiah J. [1 ]
Cordes, David B. [2 ]
Boyle, Megan M. [1 ]
Hartlieb, Karel J. [1 ]
Friedman, Douglas C. [1 ]
Slawin, Alexandra M. Z. [2 ]
Stoddart, J. Fraser [1 ]
机构：
[1] Northwestern Univ, Dept Chem, Ctr Chem Integrated Syst, Evanston, IL 60208 USA
[2] Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 41期
基金：
英国工程与自然科学研究理事会; 美国国家科学基金会;
关键词：
TEMPLATE-DIRECTED SYNTHESIS; DONOR-ACCEPTOR; MOLECULAR MECCANO; CHEMICAL TOPOLOGY; BORROMEAN RINGS; TREFOIL KNOT; STEREOCHEMISTRY;
D O I：
10.1021/ja3085115
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A donor-acceptor [3]catenane incorporating two cyclobis(paraquat-p-phenylene) rings linked together by a dinaphtho[50]crown-14 macrocycle possesses a pi-electron-deficient pocket. Contrary to expectation, negligible binding of a hexaethylene glycol chain interrupted in its midriff by a pi-electron-rich 1,5-dioxynaphthalene unit was observed in acetonitrile. However, a fortuitous solid-state superstructure of the expected 1:1 complex revealed its inability to embrace any stabilizing [C-H center dot center dot center dot O] interactions between the clearly unwelcome guest and the host reluctantly accommodating it. By contrast, in aqueous solution, the 1:1 complex becomes very stable thanks to the intervention of hydrophobic bonding.
引用
收藏
页码：17007 / 17010
页数：4
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